2,4,5-triamino-8-chloropyrimido-[4,5-b]quinoline | 830347-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,4,5-triamino-8-chloropyrimido-[4,5-b]quinoline
• 英文别名: 8-Chloropyrimido[4,5-B]quinoline-2,4,5-triamine
• CAS: 830347-32-5
• 化学式: C₁₁H₉ClN₆
• 分子量: 260.686
• InChiKey: IRNZOOZZEUKRML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(氯甲基)-1H-苯并三唑 、 2,4,5-triamino-8-chloropyrimido-[4,5-b]quinoline 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以66%的产率得到
  参考文献：
  名称：

  新型5-杂芳基氨基-2,4-二氨基-8-氯嘧啶-[4,5-b]喹啉的对接研究和开发作为潜在的抗疟药。

  摘要：

  我们使用MOE-Dock（Docking软件）来预测10种新颖且有效的5-取代的氨基-2,4-二氨基-8-氯嘧啶基-[4,5-b]喹啉（化合物IX）的结合模式抗疟疾药物开发计划。通过分析这些化合物与恶性疟原虫中存在的11种酶的活性位点之间的相互作用来完成此操作，并据此观察到与恶性疟原虫谷胱甘肽还原酶（PfGR）的有效结合。化合物IX与PfGR的结合分数也与其抗疟活性一致。然后，根据上述对接研究和该类别的药效学要求，设计并合成了三个其他类似物。

  DOI：

  10.1016/j.bmcl.2006.02.038
• 作为产物：
  描述：

  2,4-diamino-5,8-dichloropyrimido[4,5-b]quinoline 在 氨 作用下， 反应 1.0h， 生成 2,4,5-triamino-8-chloropyrimido-[4,5-b]quinoline
  参考文献：
  名称：

  Design, synthesis and evaluation of 5-substituted amino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines as novel antimalarials

  摘要：

  Novel 5-substituted amino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines were designed based on a pharmacophore developed for potent antimalarial activity using Chem-X and MOE softwares. The designed molecules were synthesized by following a novel route and were evaluated by Rane's test for blood schizonticidal activity in mice infected by Plasmodium berghei. Based on the Mean Survival Time (MST) data, of the nine compounds evaluated, three had curative potential when compared with chloroquine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.037

文献信息

• Design, synthesis and evaluation of 5-substituted amino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines as novel antimalarials
  作者：Advait A. Joshi、Sachin S. Narkhede、C.L. Viswanathan

  DOI：10.1016/j.bmcl.2004.10.037

  日期：2005.1

  Novel 5-substituted amino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines were designed based on a pharmacophore developed for potent antimalarial activity using Chem-X and MOE softwares. The designed molecules were synthesized by following a novel route and were evaluated by Rane's test for blood schizonticidal activity in mice infected by Plasmodium berghei. Based on the Mean Survival Time (MST) data, of the nine compounds evaluated, three had curative potential when compared with chloroquine. (C) 2004 Elsevier Ltd. All rights reserved.
• Docking studies and development of novel 5-heteroarylamino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines as potential antimalarials
  作者：Advait A. Joshi、C.L. Viswanathan

  DOI：10.1016/j.bmcl.2006.02.038

  日期：2006.5

  MOE-Dock (Docking software) was used to predict the binding modes of 10 novel and potent 5-substituted amino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines (compounds I-X) as part of our antimalarial drug development programme. This was done by analyzing the interaction of these compounds with the active sites of 11 enzymes present in Plasmodium falciparum and based on this, effective binding was observed

  我们使用MOE-Dock（Docking软件）来预测10种新颖且有效的5-取代的氨基-2,4-二氨基-8-氯嘧啶基-[4,5-b]喹啉（化合物IX）的结合模式抗疟疾药物开发计划。通过分析这些化合物与恶性疟原虫中存在的11种酶的活性位点之间的相互作用来完成此操作，并据此观察到与恶性疟原虫谷胱甘肽还原酶（PfGR）的有效结合。化合物IX与PfGR的结合分数也与其抗疟活性一致。然后，根据上述对接研究和该类别的药效学要求，设计并合成了三个其他类似物。